The Underwear Shoot
by Eyeseers
Summary: One particular afternoon, Oliver Otto receives steamy pics from his oldest sister's dumbfounded boyfriend, Trip Windsor. While scrolling through, the young wannabe millionaire can't resist himself as each photo gets more revealing than the last. Eventually, the cute hunky jock gets the better of him and the fun soon begins...


**Hey everybody! I hope 2019 is going just as well as it is for you! It is so nice to see you all again! I hope you have enjoyed the last chapter to Cameron and the Ochoa Boyz. Please make sure to review, comment and share your own ideas of stories that you want to be seen. You know, this is the first of many one-shots/stories coming in the following months, so enjoy them while they last. This is my first foray into ****_American Housewife_ and I hope that you guys will like it share it amongst others.**

**Enjoy!**

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_Eyeseers Inc. Presents.._

_The Underwear Shoot_

_*This is piece of_ _work is fantasy and fiction. Any copyrighted material belongs to Eyeseers __**only**__! We are in no way in_ _relation to the Disney/ABC corporation! This story contains mature content for a mature audience. We do not know any of these characters or actors' sexual orientation. The characters mentioned in this story are all above the age of eighteen. I repeat this may or may not happen in the real life of the affiliated stars. All disclaimers apply. Enjoy!_

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_Perfect! I will leave some surprise for later..._

Trip Windsor unveiled his black Tommy Hilfiger boxer brief. It's kind of ironic that's he wearing a different brand than what he was used to. He thought of certain things about models do while showcasing underwear. Of course, there's usually a lot of skin revealed during the process. Nevertheless, he never had a problem of showing his sculpted body to the public except if he's only in his undies and that's his current situation.

He had literally stripped off his clothes and teased a little as he left his jeans unbuttoned, showing a great upper view of his black boxer briefs. Trip had to show his light bush of armpit hair that guys and girls drooled over. Without Taylor Otto knowing, multiple secretly gay football players had messaged him and asked him if he wanted to 'have some fun'. He even accepted one of the player's request and claimed that he was one of the best sex romps he's ever had with anyone!

As far as he can remember, he had cum three times during that night. Visualizing from that night, he could clearly imagine his leaking cream dripping from the ass of the football player. Trip even had to clean his cum from the football player's ass with his tongue, tasting himself. It was one crazy night!

The gorgeous jock held onto his iPhone, raised it into the air and started snapping pictures of himself against his bedroom wall. He soon repositioned himself with a side movement slowly, flaunting his toned physique to the camera.

After a couple shots, Trip let his lower back rest against a roller chair he had. He then posed with an erotic look, creating some of the most steamy photos he's ever been in. A strand of his brunette hair slightly fell out of place which made his perfect look for the next few shots.

Trip continued to shift and adjust himself. He looked at the side as he flaunted his muscular front body. His hand resting on his covered thigh. The high-school jock stood up from the roller chair and placed his iPhone on-top of his dresser-drawer. He give his bicep a slight flex as he place his hand on the back of his head.

Feeling a little aroused as he felt his bulge tightening from his Tommy Hilfiger boxer briefs, Trip put on a sultry look as he posed for the iPhone. He caressed his shredded chest down to his eight-pack abs while sexually staring at the iPhone which automatically took the photos. Not wanting to shoot a load in these newly-purchased briefs, he grabbed the camera and reviewed some of the steamy photos. _These look super hot! I wonder what the reaction would be like..._Trip dumbly gazed up at the ceiling of his bedroom.

**A Few Minutes Later**

A notification had rung off in the pants pocket of young wannabe millionaire, Oliver Otto. He pulled his phone out and noticed multiple photos that had been sent to him by Trip Windsor.

"Ugh. What did that jock do this time? Did he get his hand stuck in a vase again?" Oliver groaned to himself.

The boy shuddered as remembering numerous times of helping Trip and Anna-Kat in their wild hijinks to get Taylor Back. Ever since Trip entered into his life, he has helped him understand the true meaning of family, albeit inadvertently most times. In fact, Oliver has only gotten closer to his older sister in the short time period that the gorgeous jock has been around.

"Guess I should get this over with. Let's see what Trip's been up to..."

The young classy teen opened the first message which had a series of lewd photos of a shirtless Trip modeling with Tommy Hilfiger boxer briefs and his jeans scrunched down to his ankles.

"HOLY S-...why the hell is he shirtless?!" Oliver's voice screeched. "Did he mean to send these to Taylor?"

Wondering if that was all, Oliver scrolled down and only saw more erotic steamy pics. One photo that really caught the fifteen-year-old's attention was of Trip flexing his bicep as his conical pecs and rigid eight-pack shined throughout the photo. His eyes really popped when he noticed the high-school jock's noticeably huge bulge through the tight boxer briefs. As he stopped scrolling for a moment, Oliver _really_ took in the sight of the older teen. _Oh god! Trip looks soooo sexy in these shots. Did he do them himself? Man, this guy has a talent. I knew he had a_ _irresistibly cute face, but DAMN!_

Suddenly, another message popped up on his phone. Oliver quickly clicked on the message in hopes that it was as hot and mesmerizing as the previous ones. Once it opened up, Oliver was a little disappointed that it was merely a message rather than a pic. It read:

'_If U want 2C more, cum...NOW! I'll B w8ting...'_

The younger and lanky teen's eyes widened a little at the sight of the text. A slight moan quickly escaped his plump pink lips at the realization that the beefcake's thick cock could be ramming his hole right now. After damn near moaning in ecstasy at the sight, Oliver quickly grabbed his jacket and dashed out the Otto house.

**That Same Afternoon**

Arriving at the Windsor's house, Trip had to grin when he saw the middle Otto child anxiously fidgeting as he waited for someone to answer the door. Still standing shirtless with his black Tommy Hilfiger boxer briefs, the hunky jock hurried down the stairs and opened the door to his house.

"I see that you came, if you know what I mean..." Trip smirked as he gazed into the brown eyes of the classy wannabe millionaire.

Responding without any given thought, Oliver giggled like a little schoolgirl who was talking to her crush. _Where the hell did that come from? _"Well, I didn't expect to see this from you. Maybe I underestimated you!"

"Yeah!" Trip nodded his head as his cheeky grin quickly turned into a wide smile. "What does underestimate mean?" The jock soon questioned the lanky teen.

The duo made their way towards Trip's room. At the time his parents were out of town, so the handsome football player had the whole house to himself. Instead of throwing a huge party with his other football teammates and sexy cheerleaders, he decided to spend the down time with his true best friend, Oliver Otto. He could have spent the alone time with Taylor, but she was way too busy with the Drama club to be dealing with Trip's antics.

Once they entered Trip's room, Trip flopped onto his bed while Oliver observed his new surroundings. The business savvy teen started to get a little breathless as he constantly stared at the older high-school teen. It was pretty clear to Oliver that Trip is more ripped and his muscles are well-toned than most bodies of other guys like Cooper. Smirking a little when he saw the lanky fifteen-year-old's reaction, the muscular jock lightly rubbed his hands across his god-like chest. The brown eyes of the Otto child moved as the older football player's hand did. Oliver felt his five and a half inch twitch at the fact that he could actually see Trip's ripped naked body and not fantasize what lied underneath.

Noticing that the eyes of his crush were outlining his every move, Trip traced his cute nipples and slid down to his hard clothed cock. In fact, his own eight inch cock throbbed against the bulging boxer briefs at the thought of Oliver lightly stroking himself with his lathered spit covering the shaft. Though, he had a slight internal smirk at how Taylor would react if she had seen her boyfriend with her younger brother and saw his steamy underwear shoot.

After moments of pure tension, Trip soon spoke, "Well, what are you waiting for? He questioned. "Strip down and come get this!" The beefy jock reached down and gave his firm cock a light squeeze.

Oliver's eyes widen and his mouth agaped with shock and incredulity. He was about to say something, but before he knew it he had already pounced onto the bed of the high-school football jock. To the wannabe millionaire's surprise, Trip's tender lips had already coincided with his own. Oliver knew that this was wrong and he even wanted to break the kiss, but Trip's lips felt so good on him.

The older high-school jock quickly became a dominant force as he slipped his tongue into Oliver's mouth, licking the bottom lip. By the lack of air from their airways, they broke the kiss leaving both of them panting heavily. A smug grew from Trip's pink lips as he plopped himself into the roller chair and rolled directly towards a standing Oliver.

With the classy wannabe businessman knowing full well what he wanted him to do, the muscular teen's grin only grew as he watched Oliver reaching down and grabbing onto the bottom of his Polo shirt before pulling it over his head, revealing his slim chest to the beefcake. Moaning a little at the sight of Oliver's chest, Trip could feel his hard-on squirming for a release.

Deciding to take control of the buff brunette, Oliver slowly rubbed his pale chest in the same way that the older football jock had done to him. "You like?" The fifteen-year-old teased with his usual 'Otto' smirk, as he liked to call it personally.

Trip laughed then bit his bottom lip. He stood up from the roller chair while his brown eyes dropped to Oliver's pink nipples. Due to the cold air circulating throughout the room and the erotic nature of the ripped muscle god just inches apart from his face, the nub seemed so hard and ready to be devoured. The football jock made his second move after a few seconds as he wrapped his lips around the sensitive nub, giving it a small lick.

Oliver threw his head back as soft moans escaped from his mouth. _Aah! This is too good to be true. THE Trip Windsor is sucking on my nipple!..._While sucking his nipple, Trip placed more pleasure on the younger teen as he rubbed him through his pants.

"Fuck." The middle Otto child swore. He could feel the beefy hunk's fingers indirectly jerking his dick from his pressed pants.

Soon enough, Trip pulled out from the nub with a pop. Not wanting to waste anymore time, the high-school football player rushed to undo Oliver's pants before letting them drop down to the floor. Leaving the lanky teen in his undies, the more muscular-looking teen just enjoyed the view of the average-sized tent forming in Oliver's underwear. _Awww. I remember being at that size. Maybe if little Olly grows a bit more in a few years, then he could fuck me silly..._

The jock placed his hands on both sides of the waistband of Oliver's underwear and started pulling it down, leaving it on the floor. Once the small piece of cloth uncovered the groin area, a five and a half inch cock bounced up and nearly slapped against the wannabe business's lightly defined four-pack abs. _What a good cock to suck! _Mesmerized by the wavering pale shaft, Trip got down onto his knees and darted his brown eyes sharply towards Oliver's. The dumb-founded Trip couldn't contain his excitement as he let a satisfied moan escape his lips.

Feeling uncomfortable as the cool air touched his tender chest, Oliver soon confronted the high school jock. "Stop Staring. Can you do something, please?"

"What do you want me to do?" You can tell me," Trip teasingly asked as his fingers glided across the wannabe millionaire's length.

"Please...suck my cock!" The young classy businessman shouted with such joy in his tone. He soon bit his lip after saying those words.

He regretted it.

He wanted to be the one who was sucking his eight inch monster. However, Oliver couldn't help his dominant side.

Trip teasingly looked at the younger teen as he spread Oliver's hairless legs widely to give more access to his cock and tightly-cupped balls. Noticing that the fluorescent pink head was starting to drip pre-cum, the football player licked the liquid pre-cum, getting a taste of what was to come. _If Olly's pre-cum can taste this good, then I wonder how his real load is going to taste. _The muscular and older teen started to lick the base of the young businessman's cock. Trip could literally smell the musk and sweat from Oliver's crotch.

Once the five and a half inch cock was covered in saliva, Trip returned to the mushroom head as he wrapped his pretty pink lips around it. The head felt so good and erotic. Craving more, the high school jock pushed more and more of the cock inside his mouth. He teased Oliver with his tongue swirling around the moist head as he continued to collect all of the leaking pre-cum. The pleasure soon became unbearable at this state. The gorgeous football player knows how to please a man with his mouth.

Trip didn't hesitate to push all of Oliver's cock inside his mouth, bobbing up and down in the process. With each movement, he sucks the head that pushes Oliver over the edge.

In fact, Oliver tried his best to contain his moans as he knew that he had to keep up with dominating style. As he bit his bottom lip, the coils from his stomach started to intensify.

"T-Trip, I'm gonna..." Before the young wannabe millionaire could finish what he was saying, he could feel the head of his pale cock thicken within the warm mouth of Trip Windsor.

The high school jock didn't pull off when he knew that the middle Otto child was on the verge of releasing his seed. He made sure he'd swallow all of Oliver's cum before pulling the five and a half inch cock out of his mouth with a loud pop; His saliva covered Oliver's still-erect member.

"Damn. That was-"

"Amazing!" Trip continued, finishing the young wannabe's sentence.

It was one of Oliver's weaknesses: not completing his sentences due to exhaustion. Trip smiled at him as he stood back up on his two feet and kissed him passionately. The classy fifteen-year-old could taste his own sweet and salty cum from Trip's lips. They kissed while their watery saliva exchanged through their accepting mouths. Oliver was a panting mess as the football star's pouty lips pulled away from his own.

"Well I'll be damned! That was fucking hot," Oliver regained his strength.

"We're not done yet!" Trip devilishly growled.

First, he placed his hands under the middle Otto child's thighs. Then in a blink of an eye, lifted both of Oliver's legs high into the air and spread them to the sides. The developing teen looked upon in shock at the incredible strength._ So, this is the result of Trip's mandatory football workout sessions at school..._

"Hold them for me baby," Trip commanded.

Oliver slowly placed his tender hands under his knees to keep his legs in the air. The muscular hunk couldn't help but lick his lips as he stared at him. His eyes landed directly at Oliver's hairless crack and glorious pink pucker.

"I'm going to eat you out now, okay. I am pretty sure you're going to love this Olly!" Trip squeezed the young businessman's pale butt cheeks.

The fifteen-year-old bit his thin lips as he nodded in response. His ass clenched, craving for the gorgeous stud's touch. Trip started to lick the white skin that lead towards Oliver's crack.

Oliver felt so hot. He could feel his cock starting to get hard again. _It can't be.. _During most of Oliver's private sessions, he couldn't shoot his load a second time as much as he tried. Just one orgasm would put the middle Otto child to sleep, literally!

Trip used his thick fingers to spread the wannabe millionaire's ass cheeks widely for a better view of the magestic pucker. He let his tongue fall out of his mouth and swirled it around the clenching pink hole. Feeling the fiftten-year-old shivering around his lathered tongue, the high school jock knew that he wouldn't risk pushing his appendage inside. His young play-thing was too horny at the moment. Nevertheless, Trip's tongue pushed in against the hole.

The middle Otto child closed his eyes with his mouth agaped and threw his head back. Noticing that Oliver was panting profusely as sweat began to persperate across his forehead, Trip suddenly stopped and pulled away.

"Fuck my ass with your fingers!" Oliver blurted out with pride and confidence.

Grinning at the bubbly teenager, the muscular high school jock shushed him; their lips soon reconnected once more. Oliver could barely move his body. Trip had him right where he wanted him to be.

Trip whispered into the right earlobe of the classy businessman, "That's enough for now." As Oliver seductively rode his fingers, the muscular jock suddenly pulled out his fingers at ease.

The classy wannabe millionaire was starting to get impatient but he didn't want to stop the teasing. It's making him crave more. "What the fuck?!"

"You got something to say?" Trip deathly stared at the fifteen-year-old. He smacked Oliver's thigh, making him tingle and shiver in agony.

The pale teen's face became flushed, transforming into a bright rosy red color that complimented his skin tone. Oliver tried to cover his cherubic face as he hid in embarrassment. He took a big gulp before responding to the hunky muscle-bound teen hovering over him. "T-Trip, please stop teasing me like this. You've turned me into such a mess all over your bed. I'm craving to actually feel your HUGE cock inside my tiny hole!"

As much as he wanted to hold it in, chuckles began pouring out of Trip's mouth after hearing what he just heard from the pompous Oliver Otto. After much anticipation, the high school football jock slid his boxer briefs off, fully exposing the golden teen in all of his glory. Underneath the tight boxer briefs revealed an eight and a half inch erect cock just waiting to be played with. He positioned his hard cock, lining up with Oliver's pink hole. "I'm going to fuck you now! Hard!"

The wannabe businessman lightly moaned from the deep tone of the muscular jock. He loved how Trip's playful mood could quickly turn into a devious sex god. Before the fifteen-year-old could realize what was happening, Trip had already pushed the mushroom head into Oliver's ass, plunging deep into the entrance. With the slick warmth of the older teen's cock stretching him all open in one thrust, Oliver couldn't help but shout.

"FUCK!" The younger teen gripped onto the sheets as Trip became completely buried inside him. The classy businessman took five deep breaths as his ass clenched around the football player's thick eight and a half inch shaft. Unknowingly, Oliver breathed loudly enough for Trip to hear.

_I have him right where I want him. _Upon hearing the young teen panting frantically, a smug grew from Trip's pink lips as he set the pace. With his hands firmly gripped on Oliver's hips, Trip started to thrust his veiny hips forward in a moderate pace. Expecting that his two fingers would have loosen the middle Otto child up, the high school jock quickly realizes that it didn't. He's huge! _Damn! I knew I should have used lube. We gotta make it work!..._

Oliver could feel his ass overstretching on each thrust. _Trip's bigger than all those carrots and cucumbers that I've worked into my hole. _He's already sweating from the amount of pleasure his ass is receiving despite the smoothness of the football player's movement. The wannabe millionaire nearly begged for Trip to go faster but also couldn't shake the feeling of fullness coming in and out of him in such a steady pace.

"Oh you feel so good baby," Oliver moaned.

Trip didn't know if Olly really loved this or if he was just running off emotions. In fact, he still wants to discover more of the lanky teenager. He wasn't expecting to perform kinky acts on the Otto child, but as the dominant, Trip should have something up his sleeves. Meanwhile, Oliver began to stroke his five and a half inch cock, following the rhythm of Trip's movement. Trip loves how needy Oliver is right now. Acting like a whore in front of him.

The pale teen moaned into his clenching fist, "More. I want more."

Fulfilling the teen's request, Trip started racking his hips forward, thrusting harder into the classy wannabe. The way their bodies met in each thrust nearly sent Oliver into overdrive. Him lying on his skinny back while the muscular football jock fucked him wildly is all the fifteen-year-old had wanted for so long.

"Hit me right there. Oh fuck!" Oliver continued to praise the dominating older teen. "Faster!"

His moans urge the star high school athlete to do more rough thrusts. As a response, Trip began fucking him forward relentlessly like the little bitch he was. The future businessman's slim body rocked back and forth as the handsome football player thrusted his eight and a half inches roughly against his hole. At this point, he assumed that his ass is deep red from the Windsor son's skin smacking against it.

More moans escaped from Oliver's pouty pink lips. Yet he was still begging to be fucked harder and faster. it was official: Oliver is a moaning mess. With his eyes rolling into the back of his head, the wannabe businessman wanted to be wrecked by the gorgeous and daring guy that was dating his older sister. The fat lengthy cock, that he always wanted to have in his ass, was now destroying his insides, roughly bruising him. Oliver felt his legs weaken at the sensation, but he still managed to keep it together; His knees trembled with each thrust.

Trip lowered himself down towards Oliver's level and moaned into his right earlobe, "You take me so well baby. Say my name babe."

"T-T-TRIP!" The fifteen-year-old screamed at the top of his lungs. He gripped onto the sheets with one hand while furiously stroking his five and a half inch cock with the other.

"That's right baby. Get ready to cum for me!" The chiseled teen enjoyed hearing Oliver beg in response to his dirty talk while being fucked all in all.

The brunette Otto soon gazed up at the high school jock as tears formed in his eyes from the fierce pounding. "P-Please don't stop. I'm too close to cumming!" He followed up with a loud whimper as if he was begging like a small puppy.

Oliver's five and a half inch cock was throbbing painfully from all the sensual pleasures he was taking in his ass. Keeping up with dumb and clueless facade, Trip didn't even know what he meant. In fact, the muscular football athlete went his fastest pace as it completely drove Oliver into luxurious heaven. The wet plopping sound of the older teen's veiny hips against the classy businessman was increasing with each thrust.

Suprising the younger teen and himself, Trip pulled out of the wannabe millionaire's pale ass in a sudden manner. The void of emptiness feels unbearable. Not too long after in one deep thrust, the football jock shoves his mouth-watering eight and a half inch cock back into the warmth and moves relentlessly.

Oliver wished he could do this again. Next time, up to the point when he can feel the burn from his lower spine or until Trip completely destroys his tender pink hole. The wannabe millionaire wanted to touch himself but the hunky teen hovering over him managed to reach out and grab his steel-hard five and a half inches before him.

"HOLY FUCK!" The younger teen shouted.

"It's okay bro. I've got you." Trip tried to calmly soothe the panicking Otto child. However, the classy businessman was far too gone.

"Fuck me Trip! Oh God! I'm cumming!" Oliver loudly moaned as his voice became very disoriented.

In a matter of seconds, Oliver releases his thick cum. His cock erupted as it spewed cum, smearing around Trip's hand and landing across his flat stomach. With Trip moaning loudly at the sight of Oliver's cum flying into the air and dropping onto the boy, the muscular high school jock gave his last powerful deep thrust into his hole. He rocked his veiny hips forward as his eight and a half inch cock fired a big load inside the wannabe millionaire's pale ass.

The duo both collapsed in a sweaty heap, both gasping for breath. As he panted, the star football athlete pulled his cum-slicken cock out of the fifteen-year-old's wincing hole. A loud pop soon followed. Rearranging their positions, Oliver laid down on Trip as the middle Otto child caressed his sculpted and sweaty chest. "You have nice cute nipples." The classy businessman giggled, running his finger over one of Trip's oval conical pecs.

As they caught their breath, the hunky football star picked Oliver up in a bridal style fashion and left the steamy bedroom. "I got you." Trip stared deeply into his young lover's eyes.

In fact, Trip lead him to a large bathroom with a huge shower that had glass casing surrounding the area. He slowly sat the younger teen down and turned the warm water on. As soon as the water was nice and warm, the lovable gorgeous goof stepped in followed by the rosy-cheeked Otto child.

While they washed their brunette hair and soaped up their cum coated bodies, the duo couldn't help but share one more passionate kiss. Unbeknownst to the younger teen, Trip gently grasped Oliver's soft cock in his soapy hand and stroked it. Noticing that the five and a half inch cock was becoming erect, the length fully rose within the stronger teen's grasp, throbbing between the spaces of his fingers.

"Y-You, you ruined me." Oliver said tiredly as he rest his back against the cold tile wall.

"The pleasure is truly all mine!" Trip charmed himself as he gave the tiresome Otto child a noticeable wink.

Oliver couldn't help but smile at the handsome lovable goof as he hovered over him to give the wannabe millionaire a peck on the cheek. Oliver wanted to offer Trip something dumb like more rough sex but in different positions. However, he was too exhausted at the moment. For all he knew, the pics worked on him and he wouldn't miss the next underwear shoot.

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**Thank you all for making it through this lengthy one shot! This is probably one of my longest story or chapter ever. I hope you all comment below on not just this story but for all my other stories. I appreciate each and every one of you for waiting this long to read my next story. Until the next one (or update)...**

**Eyeseers**

**(PS - Be on the lookout for new updates this summer! I know y'all can wait!)**


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